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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Guo, Qipeng Voda, Andreea S. Salim, Nisa V. Wong, Cynthia Magniez, Kevin |
| Copyright Year | 2016 |
| Abstract | We report for the first time the use of Nα-Boc-L-tryptophan for the synthesis of amphiphilic BAB triblock copolymers for potential drug delivery applications. A library of poly(Nα-Boc-L-tryptophan)-block-poly(ethylene glycol)-block-poly(Nα-Boc-L-tryptophan) (PBocLTrp-b-PEG-b-PBocLTrp) amphiphilic copolymers were synthesized through the ring opening polymerization of Nα-Boc-L-tryptophan Nα-carboxy anhydride as initiated by diamino-terminated PEG of fixed molecular weight (Mn 3350). The influence of the hydrophobic block length over self-assembly was investigated for 4 of the BAB copolymers of molecular weights varying between Mn 5000 and Mn 17 000. It was found that an increase in hydrophobic block length led to an increase in hydrodynamic size of aggregates in solution, as well as a decrease in critical micelle concentration. TEM analysis showed the formation of spherical micelles with the largest of the copolymers forming interconnected networks of spherical micelles. The influence of hydrophobic block length over the formation of secondary structure was analyzed using circular dichroism and infrared spectroscopy. Collectively we found that the presence of t-Boc protected L-tryptophan leads to the preferential formation of α-helix secondary structure through hydrogen bonding, which, in a drug delivery vehicle context, could help in controlling drug release. Also, it is believed that the use of novel Nα-Boc-L-tryptophan could improve drug stabilization in the hydrophobic core via π–π interactions between indole rings. |
| Starting Page | 24142 |
| Ending Page | 24153 |
| Page Count | 12 |
| File Format | HTM / HTML PDF |
| ISSN | 20462069 |
| Volume Number | 6 |
| Issue Number | 29 |
| Journal | RSC Advances |
| DOI | 10.1039/c6ra03718f |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | Ethylene glycol Infrared spectroscopy Tert-Butyloxycarbonyl protecting group Alpha helix Delivery (commerce) Indole Ring-opening polymerization Tryptophan Drug delivery Hydrophobe Organic acid anhydride Biomolecular structure Circular dichroism Self-assembly Critical micelle concentration Transmission electron microscopy Amphiphile Library Hydrogen bond |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry Chemical Engineering |
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